But as the Cubs head into Wednesday's series finale against the defending National League champion Los Angeles Dodgers, Maddon certainly won't complain about having the opportunity to claim a series victory.
How they had to do it, however, is a different story.
The Cubs earned a doubleheader split with a 2-1 nightcap victory after Albert Almora Jr. delivered a 10th-inning single. The win came after the Cubs blew a ninth-inning lead in Tuesday's first game, which the Dodgers rallied to win, 4-3.
Maddon expressed his displeasure with the split doubleheader format ahead of Wednesday's matinee series finale. After Monday's game was postponed due to the combination of inclement weather and electrical issues with Wrigley Field's lights, Tuesday proved to be a long day for everyone involved.
"I don't like it," Maddon said Tuesday, according to the Chicago Tribune. "I don't think it's a good idea. To be here for a noon game and then a 7 o'clock game, that's wrong. I don't think there's one player, manager, coach who thinks it's a good idea."
Maddon added: "I'm not crying. It's just true. So it works for both sides. The Dodgers have to do the same thing. I'm not just talking about us. I'd just prefer a different method over the split doubleheader to appease when the game was rained out like it was [Monday] night."
Maddon voiced his opinion ahead of Tuesday's rescheduled series opener in which Cubs reliever Justin Wilson surrendered a two-out, two-run single in the ninth inning. Wilson pitched in place of closer Brandon Morrow, who was unavailable for Tuesday's doubleheader due to back spasms. The Cubs didn't make Morrow's condition public until after Tuesday's first game when Maddon said he was holding out Morrow for precautionary reasons. Morrow told reporters he considered his availability to be day-to-day.
After offense came at a premium in Tuesday's second game, Wednesday's showdown has all the makings of a pitcher's duel.
Cubs pitcher Jon Lester (8-2, 2.28 ERA) takes the mound for the series finale looking to extend what has been a successful first half of the season. Lester has won four straight starts and has only allowed a pair of runs in three starts in June. Lester is 2-3 in seven career starts against the Dodgers.
The Dodgers will counter with Ross Stripling, who will take the mound with eyes set on his seventh straight victory. Stripling (6-1, 1.76 ERA) hasn't lost since April 30 and has struck out at least six in each of his last seven starts. Over his last six starts, Stripling has struck out 47 and walked just two.
Stripling, who will make his first career start against the Cubs on Wednesday, has taken over the role as the Dodgers ace in the place of injured Clayton Kershaw. His strong start has made him a strong contender for a place on the National League All-Star team.
"You never know if you'll have another chance in a six-, eight-, 10-year career to make an All-Star game," Stripling said recently, according to the Los Angeles Times. "I want to go out there and do my best to try and get there because it would be pretty cool."
Stripling has the vote of teammate Matt Kemp.
"He needs to be in there," Kemp said, according to the Times. "That boy is pitching his butt off. It's fun to watch."